Azo dye.



Laoro-mrnnssn Am oscAR ,GiiNTHEB, or ELJBEREEL'ID, AND ARTHUR zen-nor V'OII- "WINKEL, NE R., LBEBFELD, GERMANY, ASSIGNORS -'ro FA'RBENFABRIK'EN vonM.

rnrnnnunAYm aco oF-ELBEBFELD, GERMANY, A CORPORATION OF GERMANY.

an ortho-substituted na zihthylamin a uunin The processis carried out in an analogous AZO DYE.

933,4'57- P OaiiOn of Litters Patent. Patented SODt. 7, 1 999.

Henna wing, Application filednprill, 190 9 SeriaL-No..488,697.

T 411; wluamirit (mail concern: -'=:J!Il :a derivative of a 2.6-dia1niino-5-naphsvBe it known that..we,-.Imo1x tn Hnssn, Oscar ihol compound having the-formula: Gt'IN'rHER, and ARTHUR ZAn'r, doctors .of v X philosophy, cihemists Citizens of Gerpilai I a 5 lmpire, resii in -mt res ective ,lber e ,SO'| I-I I -Y Elberfeld, and Voliwin (e1, neaZ i'Elberfcld: KiIEgihim of f russi a, hav invi tedbnew and use u mprove nents m ,ew ;zo "olorin I Matter, of \VhlChgtheiffOllQWillg is a specii i- 10 cation. w v h Our present invention relatestothe manuv i facture and production of new secondary T l i hy'dmgul Y meanmg I AH 01 a substituted amgn0 1oup), X and disazo dyestulfs dyelng cotton from red to Y 1 f t th blue shades which are remarkable for their a so 01m ope e1 bloup S10 1 as 15 extraordinary fastness to light. j

i The new dyes are obtained by first pro- N or ducing intermediate compounds (aminoazo' (i=m n (Rand lh)=H5 compounds) from diazotlzed napht-hylamin alky] compounds, especially naphthylamin sul-. are formed.

20 fonic acid and alninonaphthol sulfonic acids 7 In order to carry out this process We can which contain. a sulfonic group in ortho-poa. 9. proceed as follows, the parts being by sition, to the amino-group, especially in \velght: 303 parts of a1pha-naphthylaminQA- alpha-beta and in beta-alpha-position and disulfonic acid are diazotized with 69 parts sultable amins,-then diazotizin these interof sodium nitrite and the necessary quantity 25 mediate products and combining the thus of hydrochloricacid and the diazo comproduced diazoazo compounds with 2-a1ninopound thus produced is then combined with 5-naphthol-7-sulfonic acid and its alkylated 156.5 parts of para-Xylidin hydrochlorid in or ary'lated derivatives and their derivatives the usual way with the addition of sodium substituted in ortho-position to the a'1nin0 acetate, the intermediate compound is reronp 0-. the 2-amino-5 11aphthol-1.7disuldissolved in wvater and is then rediazotized onic acid, the thiazol derivatives of the 2- at 15-20 (3., the diazo. compound is salted 80 amino- 5 -naphthol -7 -sulfonic acid (see out and filtered off. It is then stirred up United, States Letters Patent 795869) or the witlrwater to a paste and is added to a soimidazol derivatives of 2-a1nino-5 naphthollution of 315 parts of Q-phenylamino-E- 7- ll1f I1ic acid (see United States Letters 11a )hthol-7-sulfonic acid containing an ex- Patent the y -L2-diamin0-5- cess of sodium carbonate. The dyestufi is 85 naphthol-T-sulfonic acid. then isolated in the usual Way. It is after To produce the aminoazo compounds from being dried and pulverized in the shape of diazo compounds which combine only with its sodium salt a dark green powder soluble 40 difficulty one can make use of the'process in water with a violet-red color and soluble described in British Letters Patent 11343 of in concentrated sulfuric acid with a blue- 1899. 1 a. I green color. By reduction with stannous The new dyestnfi's are in the shape of their chlorid and hydr ri a the y s d?- alkaline salts dark powders easily soluble incomposed l naphthylamin 2.4: disulfomc 45 water,'solub1e in concentrated sulfuric acid acid, 2.5-dimethyl-l.4diaminoben e and with from a violet to blue color. {Upon re- 2- phenylamino 5-oxy-6-aminonaphthalene- 5 duction with stannouschlorid and hydroy 'I' -sulfonic acid are formed. It dyescotton chloric acid the dyestufi's are decom osed, fast violet shades.

manner on starting from other of the above mentioned nephthalene derivatives, such as 1.5-aminonaphthol-2.7-disulfonic acid etc;,

other suitable amins as middle components and other of the above mentioned end com-- ponents.

We claim: l

1. The hereiir described new azo dyestufi's obtainable by combining the diazo conipounds of aminoazo compounds which contain in the first component being-a naphthalene derivative, a negative group in ortho-position to the amino-group with the hereinbefore defined 2 amino 5 na'phthol compounds, which dyestuffs are, after being dried and pulverized, in the shape of their alkaline salts dark powders soluble in water,

soluble in concentrated sulfuric acid with from a violet to blue color; yielding upon reduction with stannous chlorid and hydrochloric acid an ortho-substituted naphthylamifi, a diamin and a derivative of a 2.6-

2.-The herein described new azo dyestufl which can be obtained from l-naphthlyaminset our hands in the presence of two subscribing witnesses.

LEOPOLD HESSE. [1,. 5.] OSCAR GUNTHER. [L. a]

ARTHUR ZART. [1,. 3.]

diamino-5-naphthol compound of the above \Vitnesses: given formula; and dyeing cotton from red Or'ro KGNIG,

C. J. WRIGHT.

to blue shades, substantially as described.

It is hereby certified that in Letters Patent No. 933,447, granted September 7, i 1909, upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld, arid Arthur Zart, of Vobwinkel, near Elberfeld, Germany, for an improvement in Azo Dyes, errors appear in the printed specification requiring correction as follows Page 1, line 67, (line 4 of the'formula,) after the symbol R, the parenthesis should be stricken out, and page 2, line 2, the word neph thalene should readhaphthalene;

and that the said Letters Patent should be read with these corrections therein that in letters Patent No. 933,447.

the same may conform to the record of the case in the Patent Ofiiceg Signed and sealed this 2nd day of November, A. D., 1909.- [SEAL.] 0. o. BILLING S, L Acting Commissioner of Patents.

manner on starting from other of the above mentioned nephthalene derivatives, such as 1.5-aminonaphthol-2.7-disulfonic acid etc;,

other suitable amins as middle components and other of the above mentioned end com-- ponents.

We claim: l

1. The hereiir described new azo dyestufi's obtainable by combining the diazo conipounds of aminoazo compounds which contain in the first component being-a naphthalene derivative, a negative group in ortho-position to the amino-group with the hereinbefore defined 2 amino 5 na'phthol compounds, which dyestuffs are, after being dried and pulverized, in the shape of their alkaline salts dark powders soluble in water,

soluble in concentrated sulfuric acid with from a violet to blue color; yielding upon reduction with stannous chlorid and hydrochloric acid an ortho-substituted naphthylamifi, a diamin and a derivative of a 2.6-

2.-The herein described new azo dyestufl which can be obtained from l-naphthlyaminset our hands in the presence of two subscribing witnesses.

LEOPOLD HESSE. [1,. 5.] OSCAR GUNTHER. [L. a]

ARTHUR ZART. [1,. 3.]

diamino-5-naphthol compound of the above \Vitnesses: given formula; and dyeing cotton from red Or'ro KGNIG,

C. J. WRIGHT.

to blue shades, substantially as described.

It is hereby certified that in Letters Patent No. 933,447, granted September 7, i 1909, upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld, arid Arthur Zart, of Vobwinkel, near Elberfeld, Germany, for an improvement in Azo Dyes, errors appear in the printed specification requiring correction as follows Page 1, line 67, (line 4 of the'formula,) after the symbol R, the parenthesis should be stricken out, and page 2, line 2, the word neph thalene should readhaphthalene;

and that the said Letters Patent should be read with these corrections therein that in letters Patent No. 933,447.

the same may conform to the record of the case in the Patent Ofiiceg Signed and sealed this 2nd day of November, A. D., 1909.- [SEAL.] 0. o. BILLING S, L Acting Commissioner of Patents.

ions in Letters Patent No 933,447.

Correct It is hvrohy (OItifiOd that in lmttors Pnhnt No. 933,447, granted Septomher 7, IJML upon H10 nppiimfion of Loopohi Hesse nnd ()srar Giinthor, of Elhnrfeld, and Arthur Znrt of Vohwinkol. mnr )ihorfold, Germany, for an improvement in Azo Dyes. orrors appnnr in tin printed hpocifhrntion requiring correction as follows: Page 1, line 67, (line 4 of :hrformnh1 nfter the symbol R, the parenthesis should he stricken out, and page 3, Ham 3, tho WON'T naphthalene should read naphthalene, nnd that the said Imtters Patnnishmlhi he read with those corrections therein that the same may conform to tho rowrd of the (Jill-5f in the Patent Office.

Signed and sealed this 2nd day of Nmemhvr, A. IL, 1909.

[snub] C. (J. BILLINGS,

4pm,; Col/m1 is'sz'onev of Patents. 

